(R,S,S)-6,9-Dimethoxy-3,3a,5,9b-tetrahydro-5-propylfuro<3,2-c><2>benzopyran-2-one | 161277-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R,S,S)-6,9-Dimethoxy-3,3a,5,9b-tetrahydro-5-propylfuro<3,2-c><2>benzopyran-2-one
• 英文别名: (3aS,5R,9bS)-6,9-dimethoxy-5-propyl-3,3a,5,9b-tetrahydrofuro[3,2-c]isochromen-2-one
• CAS: 161277-67-4
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: JJCXJOJZSSQYSV-BFQNTYOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,S,S)-6,9-Dimethoxy-3,3a,5,9b-tetrahydro-5-propylfuro<3,2-c><2>benzopyran-2-one 在 silver(II) oxide 、 jones reagent 、 硝酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 (11S,15S,17R)-4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
  参考文献：
  名称：

  Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions

  摘要：

  Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.

  DOI：

  10.1021/jo00110a017
• 作为产物：
  描述：

  1-(1-hydroxybutyl)-2,5-dimethoxybenzene 在 正丁基锂 、 mercury(II) diacetate 、 lithium chloride 、 palladium dichloride 、 barium(II) oxide 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 52.0h， 生成 (R,S,S)-6,9-Dimethoxy-3,3a,5,9b-tetrahydro-5-propylfuro<3,2-c><2>benzopyran-2-one
  参考文献：
  名称：

  Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions

  摘要：

  Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.

  DOI：

  10.1021/jo00110a017

文献信息

• Radical Conjugate Addition of Aryl-Tethered β-Alkoxyacrylates: Formal Synthesis of (±)-Frenolicin B and (±)-epi-Frenolicin B
  作者：Christopher Donner

  DOI：10.1055/s-0029-1217118

  日期：2010.2

  The radical conjugate addition of aromatic-tethered O-stannyl ketyl radicals to β-alkoxyacrylates is demonstrated for the preparation of benzopyran-γ-lactone-fused tricyclic systems. This method is then applied to the stereodivergent formal synthesis of the kinase inhibitor (±)-frenolicin B and (±)-epi-frenolicin B.

  芳香族束缚的 O-甲锡烷基自由基与 β-烷氧基丙烯酸酯的自由基共轭加成被证明可用于制备苯并吡喃-γ-内酯稠合三环系统。然后将该方法应用于激酶抑制剂 (±)-frenolicin B 和 (±)-epi-frenolicin B 的立体分歧形式合成。
• Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions
  作者：George A. Kraus、Jun Li、Mark S. Gordon、Jan H. Jensen

  DOI：10.1021/jo00110a017

  日期：1995.3

  Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.